Overwhelmed By Your Side Hustle To-Do List? We Asked the Experts to Weigh In

Overwhelmed By Your Side Hustle To-Do List? We Asked the Experts to Weigh In

My head is about to explode.

In the past few weeks of my work as a freelance writer, I’ve penned a feature story about retired NASCAR driver Dale Earnhardt Jr., done a ton of research on wearable technology for my next piece, rode my bike 250 miles across Missouri for another project, overhauled my social media strategy, hired someone to manage it, and laid the groundwork to launch an entirely new part of my career.

My to-do list is so long I’m having a hard time keeping it all straight, staying focused, figuring out what to work on, when and for how long. It’s the natural reward of working hard to create a career as a solopreneur, and I don’t think I’m alone.

I imagine many other people working for themselves face this exact conundrum. It’s a good problem to have, or at the very least it’s better than having nothing to do. The first takeaway from this has to be learning to say no, of course. That’s a way to avoid the problem in the first place, and I’ll remember it the next time things start to get crazy.

For now, I’ve got to dig into this pile of work, make sense of what’s in front of me and formulate a plan of how to get it all done. I asked experts for help in how to keep my focus, make priorities and find order amid this chaos.

Be intentional.

“It’s remarkable how long we spend working and how little time we spent choosing what to work on in the first place,” says Chris Bailey, author of three books on productivity and co-host of a podcast called Becoming Better. “What lies at the heart of productivity is intentionality. Productivity is not about doing more and more and more, faster, faster, faster. It’s about doing the right things, deliberately, and with intention.”

Bailey builds intentionality using the rule of three. On a weekly and daily basis, he picks the three most important tasks he has to do and focuses on them. “You fast forward to the end of the day in your head. Ask yourself, By the time this day is done, what three main things will I want to accomplish?”

Perhaps the toughest part of deciding what to work on is deciding what not to work on. The other 10, 12 or 15 items on my to-do list will have to wait. “This really sharpens that focus and allows you to laser in on a few things,” Bailey says.

Focusing on a narrow set of tasks and setting the rest aside gives him peace. “The path to productivity runs straight through calm,” he says.

I’ve long known that getting distracted is a major problem for me. The rule of three should help with that. One benefit of deciding which three things are most important is that when the proverbial fire breaks out in the middle of your day, you are better prepared to ascertain how crucial it is to put it out.

“It’s sometimes difficult to tell when you’re right next to it whether a fire is the size of postage stamp or the size of a bonfire,” he says. “But when you step back, you can figure out whether you need to blow it out or get a bucket of water.”

Even from a visual standpoint, a to-do list with three bullet points appears manageable. A to-do list with 20 does not. I’d much rather have the satisfaction of finishing three things than working on a dozen and completing none. As Bailey puts it: “It’s possible to be very, very busy but not really accomplish anything.”

Get clarity.

I talked to Peter Bregman, author, speaker and CEO of executive coaching company Bregman Partners, and described my struggles. As he peppered me with clarifying questions, it became obvious that one reason I couldn’t decide what to work on was that I didn’t understand how to get done what needed to be done. It was like I had all of the ingredients needed for a recipe, and had a list of instructions, but the steps weren’t in order and I didn’t know how much of each ingredient to use.

The key word was structure. As soon as Bregman said it, I knew that’s what I lacked. As a writer for three decades, I’m so accustomed to how to structure my work that I don’t even think about it. But launching my new project required a focus on structure that I didn’t realize I was missing.

To build a solid structure, Bregman suggested writing out the recipe, so to speak. At the top of a piece of paper, I should write the name of the project I wanted to start. Underneath would be the various categories I needed to work on to create that project—product, customer, sales, marketing and so on. Under each of those, I would write the tasks needed to accomplish them. “And now you have some structure to what you’re doing. It’s not just a whole bunch of things,” he says.

Know the difference between chaos and crisis.

Sometimes I get so deep inside my own head that I get lost trying to get out. I allow anxiety about the mountain ahead of me to replace the excitement I should have had for the view I would have once I climbed it.

I talked to MK Kim about this. She’s an author and motivational speaker in Korea. The pandemic forced her to shutter lucrative work giving lectures. A career she spent 30 years building disappeared when in-person events ended. “I was doomed,” says Kim, who brands herself in the U.S. as the Korean Oprah. “I was so afraid of not being able to make money, terrified of not being able to give lectures.”

She kept telling herself, I can’t give lectures. She didn’t like the sound of that; it was as if she was the bad example in one of those lectures she could no longer give. “My job is encouraging people. So if I face hardship, I have to encourage myself first,” she said. “Then I can encourage other people.”

She changed I can’t give lectures to I will not give lectures because it’s not safe. That gave her agency. She was no longer the victim. Then she told herself, I will not give lectures offline, but I will give lectures in a different way.

Her advice in navigating tumultuous times like what she just came through is to understand the difference between chaos and a crisis. If all you see in chaos is the negative—I can’t give lectures—it will seem like a crisis. But if you find the positive in it and/or look for solutions, it will become an opportunity.

She tells a story in her latest book, Reboot, about finding order amid the chaos by connecting dots of information that weren’t previously connected. The first dot was the no-contact rules across the world. The second dot was the rise in the value of online video content. The third dot was advances in artificial intelligence that broke down language barriers.

Although she could no longer give in-person lectures, the rise in video and language technology meant she easily could reach customers around the world. She launched MK University to reach non-traditional students. It has grown from 5,000 to 60,000 students. Her YouTube channel has 1.6 million subscribers. “You can make your own order in this chaos,” she says.

* * *

After I had these conversations, the chaos that prompted them continued for weeks. I actually launched the side hustle, and launching it was far more daunting than laying the groundwork to launch it.

I came home from one assignment feeling almost overwhelmed. I had to apply all three lessons—and so precisely it was almost creepy—especially knowing the difference between chaos and crisis.

For now, at least, the mountain of work remains ahead of me. I still need to be intentional, get clarity, and know the difference between chaos and crisis. But I better understand what I’m facing and how best to summit it. 

This article originally appeared in the January/February 2022 Issue of SUCCESS magazine. Photo by @peilunchen/Twenty20

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Matt Crossman is a writer based in St. Louis. He writes about sports, travel, adventure and professional development. Email him at [email protected]

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